Alkyl-dialkylaminosilanes



Patented Oct. 28, 1947 UNITED STATES PATENT mm amass: I

ALKYL-DIALKYLAMINQSILANES Oscar Kenneth Johannson, Corning, N. Y., as-

signor to Corning Glass Works, Corning, N. Y., a corporation of New York No Drawing. Application May 16, 1946, Y

Serial 180. 870,294

6 Claims. 1

This invention concerns a new class of organo silicon amines in which the silicon is linked to the nitrogen and the remaining valences of the nitrogen are linked to alkyl groups. It pertains especially to organosilicon compositions which have the general formula Rnsl.(NR'2) 4-1. wherein each R. represents an alkyl radical and each R represents an alkyl radical and n is an integer less than 4.

The organosilicon compounds which have the above general formula are many of them liquids and are readily hydrolyzable with water. Upon hydrolysis, ,hydroxyl radicals are substituted on the silicon for the dialkylamino groups. The

- hydrolyzate may then condense with the production of a siloxane, depending upon the reactivity of the silanol which is produced. This condensation reaction is a function of the number and character of organo substitutents linked to the silicon.

The organosilicon compounds of this invention are useful for such purposes as water-proofing.

The organosilicon halides have heretofore been proposed as hydrophobing agents. Since the to neutralize the hydrogen chloride. It should be noted that the reaction should be carried out under anhydrous conditions to avoid formation of siloxane.

The alkyl substituents which are linked to the silicon by carbon to silicon bonds may be either lower alkyl groups, as for example, methyl or ethyl, or they may be higher alkyl, such as octadecyl. The length of the alkyl groups linked to the nitrogen may vary. However, it is preferred that these alkyl groups contain less than 4 carbon atoms each. Ethyl radicals are preferred due to the commercial availability of diethylamine.

The following examples illustrate various com- .pounds in accordance with the invention but should not be construed as limiting the scope hereof.

Example 1 The compound (C2lI-I5)aSiN(C2H5)z was prepared as follows:

A solution of g. of triethyl silicon chloride 2 in 25 ml. of diethyl ether was added by drops to 10.3 g. of diethyl amine in 25 ml. of diethyl other at room temperature. As soon as the addition began, a white crystalline precipitate was formed. After all the chloride was added, the crystalline material was separated from the solution. There was obtained 6.9 g. of the crystalline material. The theoretical yield of diethyl amine hydrochloride is '7.2 g. On removing diethyl ether from the filtrate, 10 g. of liquid was obtained, as against a theoretical yield of 12.4. g. of the product being prepared. The liquid was fractionated. The main product was found to boil at 85-86 -C. at 12 mm. Upon analysis, this fraction was found to contain silicon in amount equivalent to 82.03% S102 (theory for the compound being prepared is Example 2 The compound (C2H5)2Sl(N(CzH5)2)2 was prepared as follows:

A slight excess over two mols of diethylamine was added to a benzene solution of one mol of diethyldichlorsilane. The diethylamine hydrochloride was filtered off and the filtrate was distilled. Two fractions were obtained. The first fraction by analysis was shown to be The second fraction was the desired diethylbisdiethylaminosilane, and had the properties and analysis shown.

Found Theoretical Boiling Point l42 C. at 50 mm Sp. G. 20 4 0.853 Ref. Index 20 Per cent N Per cent Cl (Hydrolyzable).

Example 3 The compound C1aH37Sl(N(C2I-I5) 2)3 was prepared by the same method employed in Example 2, using octadecyl silicon trichloride as the reagent. In this case, no initial chloride fraction was obtained from the filtrate. The following properties and analysis were found:

Found Theoretical Boiling Point 2l1-216 C. at 0.16-0.30

Per cent 0. 72. 5

Per cent SL- 5.6

Per cent N 8. 5

Example 4 Th compounds CH3S1(N(C2H5) 2) 3 and (CH3)2Si(N(C2H5)a)2 were prepared by the formula RnSi (NR/z) 4- in which each R represents an alkyl radical, each R represents an alkyl radical, and n represents an integer less than 4.

2. an organosilicon amine having the general formula:

RnsflNR'ah-n in which each R represents an alkyl radical containing from 1 to 18 carbon atoms, each R represents an allwl radical, and n represents an integer less than 4.

3. An organosillcon amine having the general formula:

in which each R represents an alkyl radical containing from 1 to 18 carbon atoms, R represents an ethyl radical and n represents an integer less than 4.

6. (CzHt) aSiN(C2H5) 2.

OSCAR KENNETH JOHANNSON. 

